Tazarotene

Tazarotene
Systematic (IUPAC) name
ethyl 6-[2-(4,4-dimethyl-3,4-dihydro-2H-1-benzothiopyran-6-yl)ethynyl]pyridine-3-carboxylate
Clinical data
Trade names Tazorac
AHFS/Drugs.com monograph
  • X (U.S.)
  • Prescription Only
Topical
Pharmacokinetic data
Protein binding >99%
Half-life 19 Hours
Identifiers
118292-40-3 Yes
D05AX05
PubChem CID 5381
DrugBank DB00799 Yes
ChemSpider 5188 Yes
UNII 81BDR9Y8PS Yes
KEGG D01132 Yes
ChEBI CHEBI:32184 Yes
ChEMBL CHEMBL1657 Yes
Chemical data
Formula C21H21NO2S
351.463 g/mol
 Yes (what is this?)  (verify)

Tazarotene (marketed as Tazorac, Avage, Zorac, and Fabior) is a third-generation prescription topical retinoid sold as a cream, gel, or foam. Tazarotene is a member of the acetylenic class of retinoids. This medication is approved for treatment of psoriasis, acne, and sun damaged skin (photodamage). It is commonly sold in two concentrations: 0.05% and 0.1%.

Mechanism of action

Tazarotene is a retinoid prodrug which is converted to its active form, the cognate carboxylic acid of tazarotene, by rapid deesterification in animals and man. Tazarotenic acid binds to all three members of the retinoic acid receptor (RAR) family: RARα, RARβ, and RARγ but shows relative selectivity for RARβ, and RARγ and may modify gene expression. The clinical significance of these findings is unknown.

Side effects

Common side effects include worsening of acne, increased sensitivity to sunlight, dry skin, itchiness, redness and in some cases extreme drying and cracking of skin. For most patients these side effects are uncomfortable but mild and decrease markedly after the first 2–4 weeks of use except for increased sensitivity to sunlight.

For best results dermatologists recommend applying the cream or gel once daily before bedtime after washing the face with a mild cleanser. Dermatologists recommend using a moisturizer with tazarotene so skin will not be as dry and flaky.

Uses

Tazarotene is rated pregnancy category X, and should not be used by pregnant women.

"There is limited evidence that tazarotene and isotretinoin benefit patients with moderate photodamage on the face: both are associated with skin irritation and erythema." [1]

In addition to tretinoin, which has been associated with greater skin improvements with high concentrations, tazarotene and isotretinoin creams are also found to be effective for photodamage, but at the expense of skin irritation. More evidence is needed before any recommendations can be made on oral or topical polysaccharides or hydroxy acids. Evidence from one trial suggests that the effectiveness of 0.05% tretinoin, is equivalent to the effects of 0.05% and 0.1% tazarotene.[1] However for acne vulgaris, several recent double blind studies have shown consistently superior efficacy for tazarotene and roughly equal tolerability for both treatments.[2]

"Specifically, tazarotene reduced the number of noninflammatory and inflammatory lesions at 4, 8, and 12 weeks -- all timepoints examined during treatment. Although the reduction of inflammatory lesions compared with tretinoin did not achieve statistical significance, the reduction of open comedones at 12 weeks was 65% for tazarotene vs 44% for tretinoin (P = .034). Tazarotene also proved superior in the reduction of noninflammatory lesions at 12 weeks (55% vs 42% for tretinoin, P = .042)." [2]

Notes

  1. ↑ 1.0 1.1 Samuel M, Brooke RC, Hollis S, Griffiths CE (2005). Samuel, Miny, ed. "Interventions for photodamaged skin". Cochrane Database Syst Rev (1): CD001782. doi:10.1002/14651858.CD001782.pub2. PMID 15674885.
  2. ↑ 2.0 2.1 http://www.medscape.org/viewarticle/459255_4